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St. Augustine musician Kaylee Rose signs with Nashville-based management company

By Kara Pound

Correspondent

The music business is a difficult industry to maneuver and find success in — especially for a 22-year-old female singer-songwriter. Lucky for Kaylee Rose, a St. Augustine High School graduate who moved to Nashville in August of 2014, she’s got a good team behind her including supportive parents and a new management deal with Pennington Entertainment.

Pennington is CEO of Pennington Entertainment, a full-service entertainment and management company that connects musicians to their fans. A veteran music executive, Pennington has worked with artists such as Gretchen Wilson, Big &Rich and MuzikMafia.

“It’s an amazing feeling to have someone as well-known and respected as Shawn guiding me,” Rose says. “Nobody is trying to change me or my music. The moment I walked in, I felt like I was at home. They’ve become my Nashville family.”

Rose’s full name is Kaylee Rosenberg. She was born in Miami and her family moved to St. Augustine while she was in middle school for a smaller town feel by the beach. Being the new kid in school, Rose’s father bought her a guitar to keep her occupied during the transition.

“I was annoyed that he got it,” she laughs. “He saw something in me with music before I did. He learned how to play three chords, so he could teach me. I tried formal lessons, but they didn’t really work for me. Overall, I learned everything by ear.”

Rose’s dad, Mike Rosenberg, is a teacher at Pedro Menendez High School and lifeguard for St. Johns County Marine Rescue. Her mom, Jeannie Smith-Rosenberg, works in marketing with Cobalt Communications. Over the past decade, the Rosenbergs have supported each and every one of their musician daughter’s dreams — even when she decided to move to Nashville shortly after graduating from SAHS in 2013.

“My family comes up here to visit a lot,” says Rose. “And I go down to St. Augustine every chance I get, but it’s difficult between my music career and school.”

Aside from regular gigs at iconic Nashville venues like Puckett’s, Bluebird Café and The Listening Room Café, Rose is also majoring in business through online classes at the University of Florida. “I’m essentially living a double life,” she jokes. “I’ll get my degree from my dream school while living my dream in Nashville. I’ve kind of learned how to run on no sleep, but it’s all worth it.”

Rose’s music, which is a unique mash-up of country, pop, rock and even rap, has earned her membership to esteemed organizations like Nashville Songwriters Association International, Country Music Association and BMI.

When asked about her musical heroes, the 20-something doesn’t hesitate to name Johnny Cash and Michael Jackson because of their abilities as entertainers and modern artists Sam Hunt and Kacey Musgraves for being risk-takers and not afraid to be outside of the box in a genre like country.

“I’ve had people tell me that the music that I do is three years ahead of its time here in Nashville,” Rose says. “I never wanted to change who I was as an artist and a songwriter, but it certainly gets old not having anyone see what you see. That and females typically have a harder time in this industry, that’s why having Shawn and his group behind me means so much.”

Rose was added to Pennington Entertainment’s roster Sept. 14. What that means is the Pennington team will work toward making a connection between Rose and her fans through branding, social media and touring.

“They will basically get me in front of the right people and guide me where I need help,” she says. “Shawn sees an advantage to my unique sound and doesn’t want to change what I’ve built thus far. It’s a very overwhelming feeling to have a group of people see me for me, and see what my parents always saw in me.”